Alkoxylated esteramines and salts thereof

ABSTRACT

The present invention relates to alkoxylated esteramines of Formula (I) and salts thereof. Esteramines according to the present invention may be used in cleaning composition, for example in liquid laundry detergents. They lead to improved cleaning performance of said compositions, for example when used in cold water washing conditions. They surprisingly boost grease cleaning performance of liquid laundry detergents, especially under cold water washing conditions. Whiteness is also improved. The esteramine according to the present invention show improved compatibility in liquid laundry detergent formulations.

The invention relates to alkoxylated esteramines and salts thereof.

Due to the increasing popularity of easy-care fabrics made of syntheticfibers as well as the increasing energy costs and growing ecologicalconcerns of detergent users, the once popular hot water wash has nowtaken a back seat to washing fabrics in cold water. Many commerciallyavailable laundry detergents are even advertised as being suitable forwashing fabrics at 40° C. or 30° C. or even at room temperature. Toachieve satisfactory washing result at such low temperatures, i.e.results comparable to those obtained with hot water washes, the demandson low temperature detergents are especially high.

It is known to include certain additives in detergent compositions toenhance the detergent power of conventional surfactants so as to improvethe removal of grease stains at temperatures of 60° C. and below.

U.S. Pat. No. 6,346,643 discloses a process for the preparation ofesters of poly(ethylene glycol) with amino acid hydrochlorides.

DE 2025629 discloses esters of glutamic acid and C₁₀ to C₁₈ fattyalcohols and derivatives.

WO 2007/054226 describes the use of pyroglutamic acid esters as gashydrate inhibitors. The pyroglutamic acid esters are obtained byesterification of pyroglutamic acid or glutamic acid with an alcoholcomprising 1 to 100 hydroxyl groups.

JP2003064282 discloses ligands for semiconductor particles based ontriethylene glycol C₁ to C₇ monoethers esterified with C₂ to C₂₁aminoacids.

JP2005263890 discloses esters of C₆ to C₁₀ζ- to k-amino acids ofethoxylated glycerols.

WO2003059317 describes polyethylene glyocol monomethyl or -ethyl ethersesterified with alpha-aminoacids as part of a medicinal aerosolcomposition.

There is a continuous need for cleaning compositions that remove greasestains from fabrics and other soiled materials, as grease stains arechallenging stains to remove. Conventional cleaning compositionsdirected to grease removal frequently utilize various amine compoundswhich tend to show strong negative impacts on whiteness. As aconsequence there is still a continual need for amine compounds whichprovide grease removal abilities from fabrics and other soiled materialswhich at the same time do not negatively impact clay cleaning abilitiesor whiteness. There is a need for compounds having grease cleaningabilities at low temperatures.

It was an object of the present invention to provide compounds whichcomply with the above identifies objectives and needs.

This goal was achieved by the present invention as described hereinbelow and as reflected in the claims.

Throughout this specification and the claims which follow, unless thecontext requires otherwise, the word “comprise”, and variations such as“comprises” and “comprising”, will be understood to imply the inclusionof a stated integer or step or group of integers or steps but not theexclusion of any other integer or step or group of integer or step. Whenused herein the term “comprising” can be substituted with the term“containing” or “including” or sometimes when used herein with the term“having”.

When used herein “consisting of” excludes any element, step, oringredient not specified in the claim element. When used herein,“consisting essentially of” does not exclude materials or steps that donot materially affect the basic and novel characteristics of the claim.

In each instance herein any of the terms “comprising”, “consistingessentially of” and “consisting of” may be replaced with either of theother two terms.

Generally, as used herein, the term “obtainable by” means thatcorresponding products do not necessarily have to be produced (i.e.obtained) by the corresponding method or process described in therespective specific context, but also products are comprised whichexhibit all features of a product produced (obtained) by saidcorresponding method or process, wherein said products were actually notproduced (obtained) by such method or process. However, the term“obtainable by” also comprises the more limiting term “obtained by”,i.e. products which were actually produced (obtained) by a method orprocess described in the respective specific context.

The present invention relates to alkoxylated esteramines of Formula (I)and salts thereof,

wherein independently from each othert being an integer from 1 to 100;A₁ is independently for each repetition unit t selected from the listconsisting of ethyleneoxy group, 1,2-propyleneoxy group, 1,2-butyleneoxygroup, 2,3-butyleneoxy group, i-butyleneoxy group, pentyleneoxy group,hexyleneoxy group, styryloxy group, decenyloxy group, dodecenyloxygroup, tetradecenyloxy group, and hexadecanyloxy group, wherein for tequal to 1 the oxygen atom of the A₁ group is bound to the B group andthe following A₁ group is always bound via the oxygen atom to theprevious A₁ group.

B₁ is independently selected from the group consisting of a bond, linearC₁ to C₁₂ alkanediyl groups, and branched C₁ to C₁₂ alkanediyl groups;

R₄, R₈, and R₁₂ being selected from the group consisting of H, linearalkyl, branched alkyl, and cycloalkyl;with the provisio that Z₁ is selected from the group consisting ofalanine, arginine, asparagine, aspartic acid, cysteine, glutamine,glycine, histidine, isoleucine, leucine, lysine, methionine,phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine,and a compound according to Formula (II), wherein said compoundaccording to Formula (II) connects to the compound according to Formula(I) via the bond labeled with *, with the provisio of at least one groupR₄, R₈, and/or R₁₂ containing at least 7 or more carbon atoms;

with independently from each otherw being an integer from 0 to 12;R₁₃ and R₁₄ independently for each repetition unit w being selected fromthe group consisting of H, linear alkyl, branched alkyl, and cycloalkyl;R₁₅, R₁₆, R₁₇, and R₁₈ being selected from the group consisting of H,linear alkyl, branched alkyl, and cycloalkyl.

Esteramines according to the present invention may be used in cleaningcomposition, for example in liquid laundry detergents. They lead toimproved cleaning performance of said compositions, for example whenused in cold water washing conditions. They surprisingly boost greasecleaning performance of liquid laundry detergents, especially under coldwater washing conditions. The esteramine according to the presentinvention show improved compatibility in liquid laundry detergentformulations.

In the following, the various embodiments of the present invention aredescribed in more detail:

A₁ is independently for each repetition unit t selected from the listconsisting of ethyleneoxy group, 1,2-propyleneoxy group, 1,2-butyleneoxygroup, 2,3-butyleneoxy group, i-butyleneoxy group pentenyloxy group,hexyloxy group, styryloxy group, decenyloxy group, dodecyloxy group,tetradecenyloxy group and hexadecenyloxy group, wherein for t equal to 1the oxygen atom of the A₁ group is bound to the B group and thefollowing A₁ groups are always bound via the oxygen atom to the previousA₁ group. When t is equal to or more than 2, the independently selectedA₁ either form a randomly distributed sidechain of various alkylenyloxyunits or the form a block structure with at least one alkylenyloxy grouprepeating itself at least two times, optionally followed by furtherblocks of different alkylenyloxy group repeating themselves at least twotimes.

In one embodiment A₁ is independently for each repetition unit tselected from the list consisting of ethylenoxy group, 1,2-propyleneoxygroup 1,2-1,2-propyleneoxy group, and 1,2-butylenoxy group. In anotherembodiment, A₁ forms a block of at least two ethyleneoxy groups followedby a block of at least two propylenoxy groups, optionally followed byanother block of at least two ethyleneoxy groups. In another embodiment,A₁ forms a block of at least two 1,2-propyleneoxy groups followed by ablock of at least two ethylenoxy groups, optionally followed by anotherblock of at least two 1,2-propyleneoxy groups. In another embodiment, A₁is selected from the list consisting of ethyleneoxy group,1,2-propyleneoxy group, and 1,2-butyleneoxy group in such a way that atleast one block of ethyleneoxy groups, 1,2-propyleneoxy groups, or1,2-butyleneoxy groups is formed, optionally followed by one or moreblocks of ethyleneoxy groups, 1,2-propyleneoxy groups, or1,2-butyleneoxy groups. In another embodiment, A₁ is ethyleneoxy groups.In another embodiment, A₁ is 1,2-propyleneoxy groups. In anotherembodiment, A₁ is selected in such a way that a block of one to fiveethyleneoxy groups is followed by a block of one to three propylenoxygroups followed by a block of one to five ethylenoxy groups.

In one embodiment t is in the range of from 1 to 30. In anotherembodiment t is in the range of from 1 to 20. In another embodiment t isin the range of from 2 to 10.

In one embodiment of the present invention, B₁ is selected from thegroup consisting of a bond, and linear C₁ to C₁₂ alkanediyl groups. Inanother embodiment, B₁ is selected from the group consisting of a bond,and linear C₁ to C₆ alkanediyl groups. In another embodiment, B₁ isselected from the group consisting of a bond, and linear C₁ to C₃alkanediyl groups. In another embodiment, B₁ is selected from the groupconsisting of a bond, and a C₁ alkanediyl group. In another embodimentB₁ is selected from the group consisting of a bond, and a C₁ alkanediylgroup. In another embodiment B₁ is bond.

In one embodiment of the present invention, R₄, R₈, and R₁₂ are allindependently selected from the group consisting of H, linear alkyl,branched alkyl, and cycloalkyl. In one embodiment, R₄, R₈, and R₁₂ areall independently selected from the group consisting of H, linear C₁ toC₁₂ alkyl, and C₁ to C₁₂ branched alkyl. In another embodiment, R₄, R₈,and R₁₂ are all independently selected from the group consisting of H,linear C₁ to C₆ alkyl, and C₁ to C₉ branched alkyl.

For Z₁ being selected a compound according to Formula (II), saidcompound according to Formula (II) connects to the compound of Formula(I) via the bond labeled with *,

with independently from each otherw being an integer from 0 to 12;R₁₃ and R₁₄ independently for each repetition unit w being selected fromthe group consisting of H, linear alkyl, branched alkyl, and cycloalkyl;R₁₅, R₁₆, R₁₇, and R₁₈ being selected from the group consisting of H,linear alkyl, branched alkyl, and cycloalkyl. In one embodiment of thepresent invention, R₁₃, R₁₄, R₁₅, R₁₆, R₁₇, and Rig are allindependently selected from the group consisting of H, linear C₁ to C₁₂alkyl, and C₁ to C₁₂ branched alkyl. In another embodiment, R₁₃, R₁₄,R₁₅, R₁₆, R₁₇, and R₁₈ are all independently selected from the groupconsisting of H, linear C₁ to C₆ alkyl, and C₁ to C₉ branched alkyl.

In one embodiment of the present invention Z₁ is selected from the groupconsisting of alanine, glycine, lysine, and of compounds according toFormula (II), wherein w is an integer in the range of from 1 to 4, andthe compound according to Formula (II) connects to the compoundaccording to Formula (I) via the bond labeled with *, with the provisioof at least one group R₄, R₈, and/or R₁₂ containing at least 7 or morecarbon atom. In another embodiment Z₁ is alanine. In another embodimentZ₁ is a compound according to Formula (II) with w=0 and R₁₅ to R₁₈ areall H. In another embodiment Z₁ is a compound according to Formula (II)with w=1 and R₁₃ to R₁₈ are all H. In another embodiment Z₁ is acompound according to Formula (II) with w=3 and R₁₃ to R₁₈ are all H.

In another embodiment of the present invention B₁ is selected frombranched or linear C₁- to C₁₂-alkyl and R₈ is selected from linear orbranched C₆- to C₂₃-alkyl. In another embodiment of the presentinvention B₁ is selected from branched or linear C₁- to C₁₂-alkyl and R₈is selected from linear or branched C₁- to C₃-alkyl. Another embodimentconsists of B₁ being 2-ethyl-ethandiyl and R₈ being linear C₃-alkyl.

In another embodiment of the present invention B₁ is selected frombranched or linear C₁- to C₁₂-alkyl and R₈ is selected from linear orbranched C₁- to C₃-alkyl, and Z₁ is a is a compound according to Formula(II) with w=3 and R₁₃ to R₁₈ are all H.

In another embodiment of the present invention B₁ is selected frombranched or linear C₆- to C₁₂-alkyl and R₈ is selected from linear orbranched C₁- to C₃-alkyl, t is in the range of from 1 to 10, A₁ is foreach repetition unit t ethyleneoxy group, and Z₁ is selected from thegroup consisting of alanine, a compound according to Formula (II) withw=0 and R₁₅ to R₁₈ all H, a compound according to Formula (II) with w=1and R₁₃ to R₁₈ all H, and a compound according to Formula (II) with w=3and R₁₃ to R₁₈ all H.

In another embodiment of the present invention B₁ is selected frombranched or linear C₆- to C₁₂-alkyl and R₈ is selected from linear orbranched C₁- to C₃-alkyl, R₄ and R₁₂ are selected from H and linear orbranched C₁- to C₃-alkyl, t is in the range of from 1 to 10, A₁ is foreach repetition unit t 1,2-propyleneoxy group, and Z₁ is selected fromthe group consisting of alanine, a compound according to Formula (II)with w=0 and R₁₅ to R₁₈ all H, a compound according to Formula (II) withw=1 and R₁₃ to R₁₈ all H, and a compound according to Formula (II) withw=3 and R₁₃ to R₁₈ all H.

The esteramines according to the present invention are obtained eitheras free amines, as salts thereof or as a mixture of free amines andsalts. Salts are formed by at least partial protonation of the aminegroups by an acid being a protic organic acid or a protic inorganicacid. In one embodiment, the acid for at least partial protonation ofthe amine groups is selected from the group consisting ofmethanesulfonic acid, hydrochloric acid, hydrobromic acid, sulfuricacid, phosphoric acid, citric acid, and lactic acid. In one embodiment,the acid is selected from the group of methanesulfonic acid,hydrochloric acid, and sulfuric acid. In another embodiment, the acid ismethanesulfonic acid.

Partial protonation in one embodiment is protonation of the amine groupsin the range of from 1 to 99 mol-% of all amine groups, in anotherembodiment in the range of from 10 to 90 mol-% of all amine groups, inanother embodiment in the range of from 25 to 85 mol-%, in anotherembodiment in the range of from 40 to 75 mol-% of all amine groups.

The present invention also comprises combinations of at least twoembodiments as presented herein.

The present invention also relates to a process for preparation ofesteramine or salt thereof comprises the steps of

a) Alkoxylation of an alcohol of Formula (III)

wherein independently from each otherB₁ is selected from the group consisting of a bond, linear C₁ to C₁₂alkanediyl groups, and branched C₁ to C₁₂ alkanediyl groups;R₄, R₈, and R₁₂ being selected from the group consisting of H, linearalkyl, branched alkyl, and cycloalkyl;with one or more C₂ to 016 alkylene oxide, followed byb) at least partial esterification of the alkoxylated alcohol with atleast one acid selected from the group consisting of alanine, arginine,asparagine, aspartic acid, cysteine, glutamine, glycine, histidine,isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine,threonine, tryptophan, tyrosine, valine, and acids of Formula (IV)

with w being an integer from 0 to 12,R₁₃ and R₁₄ independently for each repetition unit w being selected fromthe group consisting of H, linear alkyl, branched alkyl, and cycloalkyl;R₁₅, R₁₆, R₁₇, and Rig being selected from the group consisting of H,linear alkyl, branched alkyl, and cycloalkyl.

In one embodiment of the present invention, B₁ is selected from thegroup consisting of a bond, and linear C_(u) to C₁₂ alkanediyl groups.In another embodiment, B₁ is selected from the group consisting of abond, and linear C₁ to C₆ alkanediyl groups. In another embodiment, B₁is selected from the group consisting of a bond, and linear C₁ to C₃alkanediyl groups. In another embodiment, B₁ is selected from the groupconsisting of a bond, and a C₁ alkanediyl group. In another embodimentB₁ is a bond.

In one embodiment of the present invention, R₄, R₈, and R₁₂ are allindependently selected from the group consisting of H, linear alkyl,branched alkyl, and cycloalkyl. In one embodiment, R₄, R₈, and R₁₂ areall independently selected from the group consisting of H, linear C₁ toC₁₂ alkyl, and C₁ to C₁₂ branched alkyl. In another embodiment, R₄, R₈,and R₁₂ are all independently selected from the group consisting of H,linear C₁ to C₆ alkyl, and C₁ to C₉ branched alkyl.

Step a) Alkoxylation of Alcohol According to Formula (III) with at LeastOne C₂- to C₁₆-Akylene Oxide.

The alcohol of Formula (III) may be reacted with one single C₂- toC₁₆-alkylene oxide or combinations of two or more different C₂- toC₁₆-alkylene oxides. Using two or more different C₂- to C₁₆-alkyleneoxides, the resulting polymer can be obtained as a block-wise structureor a random structure.

The molar ratio of alcohol of Formula (III) to total alkylene oxide maybe in the range of from 1:1 to 1:400. In one embodiment, the molar ratioof the moles of hydroxyl groups of the alcohol of Formula (III) to thealkylene oxides with which the alkoxylation reaction is carried out maylie in the range of 1:1 to 1:100. In another embodiment the ratio of themoles of hydroxyl groups of the alcohol of Formula (III) to the alkyleneoxides at which the alkoxylation reaction is carried out may lie in therange of from 1:2 to 1:50, in another embodiment in the range of 1:3 to1:10.

This reaction may be undertaken generally in the presence of a catalystat a reaction temperature from about 70 to about 200° C., in anotherembodiment from about 80 to about 160° C. This reaction may be affectedat a pressure of up to about 10 bar, in another embodiment at a pressureof up to about 8 bar.

Examples of suitable catalysts comprise basic catalysts such as alkalimetal and alkaline earth metal hydroxides such as sodium hydroxide,potassium hydroxide and calcium hydroxide, alkali metal alkoxides, inparticular sodium and potassium C₁-C₄-alkoxides, such as sodiummethoxide, sodium ethoxide and potassium tert-butoxide, alkali metal andalkaline earth metal hydrides such as sodium hydride and calciumhydride, and alkali metal carbonates such as sodium carbonate andpotassium carbonate. In one embodiment, alkali metal hydroxides areused. In another embodiment, potassium hydroxide and sodium hydroxideare used. Typical use amounts for the base are from 0.01 to 10% byweight, in particular from 0.05 to 2% by weight, based on the totalamount of alcohol and C₂- to C₁₆-alkylene oxide.

Step b) Esterification

The esterification reaction may be performed as known in the art. Aninorganic or organic protic acid may be added to the product of step a).The molar ratio of amino acid to hydroxyl groups of the alkoxylatedalcohol of step a) is 0.8:1 to 1:1.5. In one embodiment, the process iscarried out with the molar ratio of the acid to the hydroxyl groups ofthe alkoxylated alcohol of step a) is in the range of from 0.1:1 to 1:1.Reaction temperatures may be from 50° C. to 200° C., in anotherembodiment from 80° C. to 160° C. The reaction may be affected byapplying vacuum from 1000 mbar to 1 mbar, in another embodiment from 500mbar to 5 mbar. Reaction times may be from 2 to 48 hours. Suitablesolvents for the reaction may be water, toluene, xylene.

The effects for laundry as described and exemplified herein may beextrapolated to personal care applications.

The esteramines and salts thereof can be used in applications inpersonal care, as curing agent for epoxy resins, as reactant in theproduction of polymers, in polyurethanes, polyureas, or as thermoplasticpolyamide adhesives. The can also be used in shampoo or body washformulations. The esteramines and salts thereof may be included inpersonal care composition.

Methods

¹H NMR measured in MeOD with Bruker Avance 400 MHz spectrometer.pH is measured in 10% aqueous solution.Hydroxyl values are measured according to DIN 53240-1.Molecular weight of polyalkylene oxides (e.g. polyethylene glycol) iscalculated from the measured hydroxyl values by following formula:

Molecular weight[g/mol]=1000/(hydroxyl value[mgKOH/g]/56.11)×hydroxylgroups per molecule

EXAMPLES Example 1: 2-Propylheptanol, Ethoxylated with 3 Mole EthyleneOxide, Ester with 6-Amino Hexane Acid, Methane Sulfonic Acid Salt

In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet,dropping funnel, and stirrer, 58.1 g 2-Propylheptanol, ethoxylated with3 mole ethylene oxide and 26.2 g 6-amino hexane acid are placed andheated to 90° C. To the mixture 19.6 g methane sulfonic acid is addedwithin 10 minutes. The reaction mixture is heated to 130° C. and isstirred for 0.5 hours at 130° C. Vacuum (2 mbar) is applied and thereaction mixture is stirred for additional 10 hours at 130° C. 90.5 g ofa light brown solid is obtained. ¹H-NMR in MeOD indicates completeconversion to 6-amino hexane acid acid—triethylene glycol2-propyl-heptylether ester as methane sulfonic acid salt.

Example 2: C₁₃—Oxoalkohol Ethoxylated with 3 Mole Ethylene Oxide, Esterwith 6-Amino Hexane Acid, Methane Sulfonic Acid Salt

In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet,dropping funnel, and stirrer, 65.93 g C₁₃ oxoalkohol ethoxylated with 3mole ethylene oxide and 26.23 g 6-amino hexane acid are placed andheated to 90° C. To the mixture 19.6 g methane sulfonic acid is addedwithin 10 minutes. The reaction mixture is heated to 135° C. and isstirred for 7.0 hours at 135° C. Vacuum (5 mbar) is applied and thereaction mixture is stirred for additional 3 hours at 130° C. 101.95 gof a light brown solid is obtained. ¹H-NMR in MeOD indicates completeconversion to 6-amino hexane acid acid—triethylene glycol C₁₃-oxoalkoholester as methane sulfonic acid salt.

Example 3

3a: C12/C14 fatty alcohol, alkoxylated with 2 mol propylene oxide and 2mol ethylene oxide In a 2 I autoclave 573.6 g C12/C14 fatty alcohol and2.4 g potassium tert.-butylate are placed and the mixture is heated to140° C. The vessel is purged three times with nitrogen and 348.5 gpropylene oxide is added within 5 h. The mixture is stirred foradditional 6 h, followed by the addition of 264.3 g ethylene oxidewithin 5 h. To complete the reaction, the mixture is allowed topost-react for additional 6 h at 140° C. The reaction mixture wasstripped with nitrogen and volatile compounds were removed in vacuo at80° C. After filtration 1178.0 g of a light yellowish oil was obtained(hydroxy value: 141.8 mgKOH/g).

3b: C12/C14 fatty alcohol, alkoxylated with 2 mol propylene oxide and 2mol ethylene oxide, ester with 6-amino hexane acid, methane sulfonicacid salt

In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet,dropping funnel, and stirrer, 59.3 g C12/C14 fatty alcohol, alkoxylatedwith 2 mol propylene oxide and 2 mol ethylene oxide and 17.9 g 6-aminohexane acid are placed and heated to 60° C. To the mixture 13.4 gmethane sulfonic acid is added within 10 minutes. The temperature isallowed to rise to 70° C. during the addition. The reaction mixture isheated to 130° C. and is stirred for 13 hours at 130° C. Volatilecompounds are removed in vacuo (2 mbar) at elevated temperature (135°C.) and 81.0 g of a light brown solid is obtained. ¹H-NMR in MeODindicates complete conversion to C₁₂/C₁₄ fatty alcohol, alkoxylated with2 mol propylene oxide and 2 mol ethylene oxide, ester with 6-aminohexane acid, methane sulfonic acid salt.

Example 4

4a 2-ethyl-hexanol, alkoxylated with 2 mol propylene oxide and 2 molethylene oxide

In a 2 I autoclave 390.7 g 2-ethylhexanol and 2.0 g potassiumtert.-butylate are placed and the mixture is heated to 140° C. Thevessel is purged three times with nitrogen and 348.5 g propylene oxideis added within 4 h. The mixture is stirred for additional 6 h, followedby the addition of 264.3 g ethylene oxide within 3 h. To complete thereaction, the mixture is allowed to post-react for additional 6 h at140° C. The reaction mixture was stripped with nitrogen and volatilecompounds were removed in vacuo at 80° C. 1024.0 g of a light yellowishoil was obtained (hydroxy value: 164.0 mgKOH/g).

4b: 2-ethylhexanol, alkoxylated with 2 mol propylene oxide and 2 molethylene oxide, ester with 6-amino hexane acid, methane sulfonic acidsalt

In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet,dropping funnel, and stirrer, 50.2 g 2-ethylhexanol, alkoxylated with 2mol propylene oxide and 2 mol ethylene oxide and 17.9 g 6-amino hexaneacid are placed and heated to 60° C. To the mixture 13.4 g methanesulfonic acid is added within 10 minutes. The temperature is allowed torise to 70° C. during the addition. The reaction mixture is heated to130° C. and is stirred for 13 hours at 130° C. Volatile compounds areremoved in vacuo (2 mbar) at elevated temperature (135° C.) and 72.0 gof a light brown solid is obtained. ¹H-NMR in MeOD indicates completeconversion to 2-ethylhexanol, alkoxylated with 2 mol propylene oxide and2 mol ethylene oxide, ester with 6-amino hexane acid, methane sulfonicacid salt.

Example 5

5a: 2-propylheptanol, alkoxylated with 2 mol propylene oxide and 2 molethylene oxide

In a 2 I autoclave 474.0 g 2-ethylhexanol and 2.4 g potassiumtert.-butylate are placed and the mixture is heated to 140° C. Thevessel is purged three times with nitrogen and 348.5 g propylene oxideis added within 4 h. The mixture is stirred for additional 6 h, followedby the addition of 264.3 g ethylene oxide within 3 h. To complete thereaction, the mixture is allowed to post-react for additional 6 h at140° C. The reaction mixture was stripped with nitrogen and volatilecompounds were removed in vacuo at 80° C. 1065.0 g of a light yellowishoil was obtained (hydroxy value: 152.0 mgKOH/g).

5b: 2-propylheptanol, alkoxylated with 2 mol propylene oxide and 2 molethylene oxide, ester with 6-amino hexane acid, methane sulfonic acidsalt

In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet,dropping funnel, and stirrer, 59.8 g 2-propylheptanol, alkoxylated with2 mol propylene oxide and 2 mol ethylene oxide and 19.7 g 6-amino hexaneacid are placed and heated to 60° C. To the mixture 14.7 g methanesulfonic acid is added within 10 minutes. The temperature is allowed torise to 70° C. during the addition. The reaction mixture is heated to130° C. and is stirred for 5 hours at 130° C. Then, vacuum is applied(800 mbar) and the mixture is stirred for 2 hours under theseconditions. Volatile compounds are removed in vacuo (2 mbar) at elevatedtemperature (140° C.) and 86.9 g of a light brown solid is obtained.¹H-NMR in MeOD indicates complete conversion to 2-propylheptanol,alkoxylated with 2 mol propylene oxide and 2 mol ethylene oxide, esterwith 6-amino hexane acid, methane sulfonic acid salt.

Example 6

6a: 2-ethyl-hexanol, ethoxylated with 1 mol ethylene oxide

In a 2 I autoclave 651.1 g 2-ethylhexanol and 1.74 g potassiumtert.-butylate are placed and the mixture is heated to 140° C. Thevessel is purged three times with nitrogen and 220.3 g ethylene oxide isadded within 4 h. The mixture is stirred for additional 5 h at 140° C.to complete the reaction. The reaction mixture was stripped withnitrogen and volatile compounds were removed in vacuo at 80° C. 870.0 gof a light yellowish oil was obtained (hydroxy value: 321.0 mgKOH/g).

6b: 2-ethylhexanol, ethoxylated with 1 mol ethylene oxide, ester with6-amino hexane acid, methane sulfonic acid salt

In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet,dropping funnel, and stirrer, 38.3 g 2-ethylhexanol, ethoxylated with 1mol ethylene oxide and 26.2 g 6-amino hexane acid are placed and heatedto 60° C. To the mixture 19.6 g methane sulfonic acid is added within 10minutes. The temperature is allowed to rise to 70° C. during theaddition. The reaction mixture is heated to 130° C. and is stirred for 4hours at 130° C. Vacuum is applied and volatile compounds are removed invacuo (5 mbar) at elevated temperature (135° C.) for 2 hours. 72.0 g ofa light brown solid is obtained. ¹H-NMR in MeOD indicates completeconversion to 2-ethylhexanol, ethoxylated with 1 mol ethylene oxide,ester with 6-amino hexane acid, methane sulfonic acid salt.

Example 7

7a: 2-propylheptanol, ethoxylated with 1 mol ethylene oxide

In a 2 I autoclave 794.0 g 2-propylheptanol and 2.0 g potassiumtert.-butylate are placed and the mixture is heated to 140° C. Thevessel is purged three times with nitrogen and 220.9 g ethylene oxide isadded within 4 h. The mixture is stirred for additional 5 h at 140° C.to complete the reaction. The reaction mixture was stripped withnitrogen and volatile compounds were removed in vacuo at 65° C. 1010.0 gof a light yellowish oil was obtained (hydroxy value: 275.0 mg KOH/g).

7b: 2-propylheptanol, ethoxylated with 1 mol ethylene oxide, ester with6-amino hexane acid, methane sulfonic acid salt

In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet,dropping funnel, and stirrer, 44.5 g 2-propylheptanol, ethoxylated with1 mol ethylene oxide and 26.2 g 6-amino hexane acid are placed andheated to 60° C. To the mixture 19.6 g methane sulfonic acid is addedwithin 10 minutes. The temperature is allowed to rise to 70° C. duringthe addition. The reaction mixture is heated to 130° C. and is stirredfor 4 hours at 130° C. Vacuum is applied and volatile compounds areremoved in vacuo (4 mbar) at elevated temperature (135° C.) for 6 hours.80.0 g of a light brown solid is obtained. ¹H-NMR in MeOD indicatescomplete conversion to 2-propylheptanol, ethoxylated with 1 mol ethyleneoxide, ester with 6-amino hexane acid, methane sulfonic acid salt.

Comparative Example 1: Butyltriglycol Ester with 6-Amino Hexane Acid,Methane Sulfonic Acid Salt

In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet,dropping funnel, and stirrer, 64.39 g butyltriglycol and 39.35 g 6-aminohexane acid are placed and heated to 90° C. To the mixture 29.4 gmethane sulfonic acid is added within 10 minutes. The reaction mixtureis heated to 135° C. and is stirred for 4 hours at 135° C. Vacuum (5mbar) is applied and the reaction mixture is stirred for additional 13.5hours at 130° C. 122.0 g of a light brown solid is obtained. ¹H-NMR inMeOD indicates complete conversion to 6-amino hexane acid acidbutyltriglycol ester as methane sulfonic acid salt.

Comparative Example 2: Polyethylene Glycol, M_(w) Approx. 200 g/Mol;Ester with 6-Amino Hexane Acid, Methane Sulfonic Acid Salt

In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet,dropping funnel, and stirrer, 30.0 g polyethylene glycol (M_(w) approx.200 g/mol) and 39.35 g 6-amino hexane acid are placed and heated to 90°C. To the mixture 29.4 g methane sulfonic acid is added within 10minutes. The reaction mixture is heated to 135° C. and is stirred for 4hours at 135° C. Vacuum (5 mbar) is applied and the reaction mixture isstirred for additional 22 hours at 135° C. 97.0 g of a light brown solidis obtained. ¹H-NMR in MeOD indicates complete conversion to 6-aminohexane acid acid polyethylene glycol ester as methane sulfonic acidsalt.

Example 8 Use as Additives in Detergents

Technical stain swatches of blue knitted cotton containing Bacon Greasewere purchased from Warwick Equest Ltd. The stains were washed for 30min in a launder-o-meter (manufactured by SDL Atlas) at room temperatureusing per canister 500 mL of washing solution, 20 metal balls andballast fabrics. The washing solution contained 5000 ppm of detergentcomposition DC1 (table 1). Water hardness was 2.5 mM (Ca²⁺: Mg²⁺ was4:1). Additives were added to the washing solution of each canisterseparately and in the amount as detailed below. After addition the pHvalue was re-adjusted to the pH value of washing solution withoutadditive.

Standard colorimetric measurement was used to obtain L*, a* and b*values for each stain before and after the washing. From L*, a* and b*values the stain level were calculated as color difference ΔE(calculated according to DIN EN ISO 11664-4) between stain and untreatedfabric.

Stain removal from the swatches was calculated as follows:

$\begin{matrix}{{Stain}\mspace{14mu} {Removal}\mspace{14mu} {Index}} \\{({SRI}) =}\end{matrix}\frac{{\Delta \; E_{initial}} - {\Delta \; E_{washed}}}{\Delta \; E_{initial}} \times 100$

ΔE_(initial)=Stain level before washingΔE_(washed)=Stain level after washing

Stain level corresponds to the amount of grease on the fabric. The stainlevel of the fabric before the washing (ΔE_(initial)) is high, in thewashing process stains are removed and the stain level after washing issmaller (ΔE_(washed)) The better the stains have been removed the lowerthe value for ΔE_(washed) will be and the higher the difference will beto ΔE_(initial). Therefore, the value of stain removal index increaseswith better washing performance.

TABLE 1 Detergent composition DC1 Ingredients of liquid detergentpercentage composition DC1 by weight n-C₁₀-C₁₃-alkylbenzene sulfonicacid 5.3 coconut C₁₂-C₁₈ fatty acid 2.4 sodium laureth sulfate + 2 EO7.7 potassium hydroxide 2.2 C13C15-oxo alcohol + 7 EO 5.4 1,2 propyleneglycol 6 ethanol 2 water pH of detergent To Balance composition DC1 =8.0

TABLE 2 Washing Experiment with Example 2 SRI, Bacon Graese CleaningWithout additive 26.1 Example 2: C₁₃ Oxoalkohol ethoxylated 31.9 with 3mole ethylene oxide, ester with 6-amino hexane acid, methane sulfonicacid salt; 0.045 g per wash Example 1: C₁₀-Guerbetalkohol 31.8(2-Propylheptanol) with 3 mole ethylenoxide, ester with 6-amino hexaneacid, methane sulfonic acid salt; 0.046 g per wash Comparitive example1: Butyltriglycol 28.0 ester with 6-amino hexane acid, methane sulfonicacid salt; 0.049 g per wash Comparitive example 2: Polyethylenglycol,28.1 M_(w) approx. 200 g/mol; ester with 6-amino hexane acid, methanesulfonic acid salt; 0.057 g per wash

TABLE 3 Washing Experiment with Example 5b: 2-propylheptanol,alkoxylated with 2 mol propylene oxide and 2 mol ethylene oxide, esterwith 6-amino hexane acid, methane sulfonic acid salt SRI, Bacon GraeseCleaning Without additive 8.5 Example 5b: 2-propylheptanol, alkoxylated17.5 with 2 mol propylene oxide and 2 mol ethylene oxide, ester with6-amino hexane acid, methane sulfonic acid salt; 0.099 g per wash

Use as Additives in Detergents

Technical stain wfk20D (polyester/cotton 65/35, soil:pigment/sebum) fromwfk Testgewebe GmbH, was used. Washing procedure and determination ofstain removal index was followed as described above but with 1584 ppm ofdetergent composition 2 (table 4). The pH of the washing solution priorto washing with and without additives was adjusted in each case topH=8.0.

TABLE 4 Detergent composition DC2 Ingredients of liquid detergentpercentage composition DC2 by weight linear C_(11.8)-alkylbenzenesulfonic acid 17.6 C12-C15 alkyl ethoxy (1.8) sulfate 4.4 C12-C14alcohol + 9 ethylene oxide 0.9 C12-C18 fatty acid 1.1 C12-C14 amineoxide 0.8 Chelant 2.8 Solvent 14.8 brightener 0.2 sodium hydroxide 1.9Water To Balance

1. An esteramine of Formula (I) or salt thereof,

wherein independently from each other t being an integer from 1 to 100;A₁ is independently for each repetition unit t selected from the listconsisting of ethyleneoxy group, 1,2-propyleneoxy group, 1,2-butyleneoxygroup, 2,3-butyleneoxy group, i-butyleneoxy group, pentyleneoxy group,hexyleneoxy group, styryloxy group, decenyloxy group, dodecenyloxygroup, tetradecenyloxy group, and hexadecanyloxy group, Wherein for tequal to 1 the oxygen atom of the A₁ group is bound to the B group andthe following A₁ group is always bound via the oxygen atom to theprevious A₁ group; B₁ is independently from each other selected from thegroup consisting of a bond, linear C₁ to C₁₂ alkanediyl groups, andbranched C₁ to C₁₂ alkanediyl groups; R₄, R₈, and R₁₂ being selectedfrom the group consisting of H, linear alkyl, branched alkyl, andcycloalkyl; with the provisio that Z₁ is selected from the groupconsisting of alanine, arginine, asparagine, aspartic acid, cysteine,glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine,phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine,and a compound according to Formula (II), wherein said compoundaccording to Formula (II) connects to the compound according to Formula(I) via the bond labeled with *, with the provisio of at least one groupR₄, R₈, and/or R₁₂ containing at least 7 or more carbon atoms;

with independently from each other w being an integer from 0 to 12; R₁₃and R₁₄ independently for each repetition unit w being selected from thegroup consisting of H, linear alkyl, branched alkyl, and cycloalkyl;R₁₅, R₁₆, R₁₇, and R₁₈ being selected from the group consisting of H,linear alkyl, branched alkyl, and cycloalkyl.
 2. The salt of esteramineaccording to claim 1, wherein the salt is formed by at least partialprotonation of the amine group by an acid being a protic organic orinorganic acid.
 3. The salt of esteramine according to claim 1, whereinthe salt is formed by at least partial protonation of the amine group byan acid being selected from the group consisting methanesulfonic acid,hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid,citric acid and lactic acid.
 4. The esteramine or salt thereof accordingto claim 1, wherein A₁ is independently for each repetition unit tselected from the list consisting of ethyleneoxy group, 1,2-propyleneoxygroup, and 1,2-butyleneoxy group.
 5. The esteramine or salt thereofaccording to claim 1, wherein Z₁ is selected from the group consistingof alanine, glycine, lysine, and a compound according to Formula (II),wherein w is an integer in the range of from 1 to 4, and wherein thecompound according to Formula (II) connects to the compound according toFormula (I) via the bond labeled with *, with the provisio of at leastone group R₄, R₈, and/or R₁₂ containing at least 7 or more carbon atoms.6. A process for preparation of the esteramine or salt thereof accordingto claim 1, comprising the steps of a) Reacting an alcohol according toFormula (III)

wherein independently from each other B₁ is selected from the groupconsisting of a bond, linear C₁ to C₁₂ alkanediyl groups, and branchedC₁ to C₁₂ alkanediyl groups; R₄, R₈, and R₁₂ being selected from thegroup consisting of H, linear alkyl, branched alkyl, and cycloalkyl;with one or more C₂ to C₁₆ alkylene oxide, followed by b) at leastpartial esterification of the alkoxylated alcohol with at least onecompound selected from the group consisting of alanine, arginine,asparagine, aspartic acid, cysteine, glutamine, glycine, histidine,isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine,threonine, tryptophan, tyrosine, valine, acids according to Formula(IV), and salts thereof;

with w being an integer from 0 to 12, R₁₃ and R₁₄ independently for eachrepetition unit w being selected from the group consisting of H, linearalkyl, branched alkyl, and cycloalkyl; R₁₅, R₁₆, R₁₇, and R₁₈ beingselected from the group consisting of H, linear alkyl, branched alkyl,and cycloalkyl.
 7. The process according to claim 6, wherein the molarratio of alcohol according to Formula (III) to total C₂ to C₁₂ alkyleneoxide is in the range of from 1:1 to 1:400.
 8. The process according toclaim 6, wherein the molar ratio of the acid to the hydroxyl groups ofthe alkoxylated alcohol is in the range of from 0.1:1 to 1:1.
 9. Use ofthe esteramine or salt thereof according to claim 1 in personal care, ascuring agent for epoxy resins, as reactant in the production ofpolymers, in polyurethanes, polyureas, or as thermoplastic polyamideadhesives.
 10. Use of the esteramine or salt thereof according to claim9 in shampoo or body wash formulations.
 11. A personal care compositioncomprising the esteramine or salt thereof according to claim 1.